Val d’Orcia Tot. 275 km – 171 miles

Medieval castles, winding hills, ancient villages, isolated farmhouses, cypress avenues, fabulous vineyards and olive groves, and fields of wheat the color of gold-these are just some of the elements that make up the fantastic and harmonious landscapes of the Val d’Orcia. Crisscrossed by the Orcia River, from which the valley takes its name, this beautiful region in southern Tuscany runs along the provinces of Siena and Grosseto. The entire area is now a protected park, and has been recognized as a UNESCO World Heritage Site since 2004. The absolute protagonist of the Val d’ Orcia is in fact a still unspoiled and beautiful nature, with ever-changing colors according to the different seasons. There are very few other places capable of impressing the tourist so deeply. It is a land with an almost surreal and suspended atmosphere, which has also given rise to the most precious and appreciated Italian wines: the Brunello di Montalcino, Rosso Orcia and other fabulous wines with the DOCG designation.

The beautiful landscapes of the Val d’Orcia, which inspired many Renaissance painters, are dotted with many small villages, castles, abbeys, and hamlets, each with its own incredible history. Time still passes slowly here:       

  • Montalcino
  • San Quirico d’Orcia
  • Bagno Vignoni
  • Chianciano Terme
  • Montepulciano
  • Monticchiello
  • Pienza

Montalcino 

Famous throughout the world for its exquisite Brunello wine, the medieval village of Montalcino is one of the landmarks of the Val d’Orcia. Behind mighty defensive walls is a charming historic center characterized by parallel pedestrian streets set on various levels against the hillside with stairways connecting them in a continuous up and down of narrow streets, among which one can discover breathtaking views and architectural gems.

Prominent among these are the 13th-century Palazzo Comunale, with its tall clock tower, the 14th-century Church of St. Augustine, the neoclassical Duomo and Sanctuary of the Madonna del Soccorso, and the Church of St. Egidio.

Moving only a short distance from the town of Montalcino, one also encounters sacred places such as the Abbey of Sant’Antimo, dating back to the 12th century and considered among the finest examples of Romanesque architecture in Italy. 

One of the most fun and unusual activities you can do in the autumn in the countryside around Montalcino is to join a truffle and porcini mushroom hunting expedition.        

San Quirico d’Orcia

The beautiful village of San Quirico d’ Orcia was built on top of a small hill, above the remains of the ancient village of Osanna halfway between two other famous villages of the Val d’ Orcia: Montalcino and Pienza. Because of its elevated position, it offers breathtaking views of the typical landscapes of the Val d’Orcia. Just before arriving in San Quirico driving along the SS2 from Siena, look to the right just after a long bridge: do you recognize that group of cypress trees on the side of the hill? Yes, they are the most photographed trees in Tuscany!   

Bagno Vignoni

Bagno Vignoni is truly unique: nowhere else in Italy will you find a pool, located in the central square, filled with hot thermal water: 49 meters long and 29 meters wide, this Renaissance-era square was built exactly above the original source of thermal water, the same source that the Romans also used.  

Chianciano Terme

Chianciano Terme, one of Europe’s best-known spa towns, straddles the Val d’Orcia and the Valdichiana, in a perfect location for enjoying some of Tuscany’s most renowned beauty. Chianciano knows how to fascinate visitors both for its ancient municipal core and for its spa town, which is rich in mineral waters with curative action. Old Chianciano is protected by solid walls and is connected to the new part through Viale della Libertà . Once you reach the center, it is certainly worth visiting the imposing Castle of the Counts Manenti, known as the Monastery, and the beautiful Clock Tower.  

Montepulciano

Perched on a hilltop in southern Tuscany and not far from Siena, Montepulciano is a medieval town of rare beauty that is definitely worth a visit! A unique village with elegant Renaissance palaces, ancient churches, beautiful squares and small hidden corners. From Montepulciano, there is also a fabulous and boundless view of the Val d’Orcia and Val di Chiana.  

Monticchiello

This small town already in Etruscan and Roman times was a meeting place of routes that connected centers and communities in the area. It still retains the austere features of medieval fortresses, contrasting sharply with the Renaissance picture offered to us by Pienza. The strong city walls and the cassero tower that towers over the hill are signs of the village’s intense past, a bulwark of the defensive system of the Republic of Siena.       

Pienza

It is considered among the most beautiful villages ever and rightfully included in the UNESCO World Heritage List. Pienza and all its surrounding countryside offer dreamlike scenery with breathtaking views, soft hills, roads bordered by rows of tall cypress trees while the enchanting historic center was knowingly designed and built to make it the ideal city of the Italian Renaissance.